TWBDTT: Rias Bonus Episode
by BLS91090
Summary: This one-shot is an alternate beginning to "Things Will Be Different This Time", in which Rias goes for Issei first, instead of Akeno. Based on the first episode of Season 2 of the anime series, as well as the light novel. Updated in October 2017. Rated M for language, adult content and a lemon.


Issei Hyoudou suddenly awoke after a dream, in bed with a large pair of breasts right in his face! "Why am I seeing boobs first thing in the morning?!" He could feel a soft sensation from the left side of his body. _'Right in front of my eyes are two floating soft and white round-shaped objects! What a view this is!'_

The girl using him as a hug pillow was none other than the gorgeous Rias Gremory, the next heiress of the House of Gremory. He had ended up sleeping soundly in her gentle embrace during the night. She loved him very much and was willing to do anything with him.

In response, Issei would do anything to protect her, as he loved her just as much as she loved him. _'It's my healing source to sleep by sinking my face in that voluptuous oppai...'_ She was sleeping peacefully, completely naked, while snuggling Issei close to her. ' _So soft! Buchou's breasts are the best!'_ She then brought Issei's face to her breasts as she slept. ' _Aaaah, I really am loving Buchou's oppai….'_ His arm was being hugged by Rias and his hand was squeezed in her nice thighs. _'I really want to rub them and suck on them!'_

Beautiful. That's the only word to describe her in one word. That's the only word you need to describe her. She is definitely beautiful. But she is too beautiful.

Issei could feel the sensation of Rias' breasts with his nose. _'I'm loving Buchou's warmth. This is really the best…burying my face in her bosom! Truly, Buchou's breast pillow is the best!'_ Being the pervert that he was, Issei figured that this was a good time to execute something devious. He reached out both hands to squeeze the two enormous orbs before him. "I suppose that I could _accidentally_ touch them..."

Suddenly, Rias awoke. "Good morning, Ise."

This startled Issei. "Ah! I mean, uh, yeah... good morning." He wanted to ask her something. "So what's the deal here, exactly?"

"I'm sorry. I saw that you were sleeping, so I just decided to let myself in. I felt like using you as a hug pillow." The crimson haired beauty smiled warmly. She then hugged the left side of his body even stronger.

"O-Oh I see..." Issei had no objections, of course.

"Tell me about the dreams you had." Rias was drawing circles on his chest with the tip of her finger.

Issei enjoyed the sensation. He shivered a little, but told her anyway. "Well..." He went on for a few minutes about boring-ass dreams.

Rias giggled. "That's very interesting." She put her face closer to his and kissed his nose.

"Yeah, well...what are you gonna do?" Issei chuckled a little.

Rias looked into Issei's eyes. "Ise, we still have some time. What should we do?" Rias leaned over him with a sexy face and naughty voice. "Perhaps doing something sexy would help deepen communication with my adorable servant." She then kissed Issei on the cheeks a bunch.

Issei was at a loss for words. _'W-Why does Buchou adore me so much!? Is it just me or has she started to adore me even more after my big battle with Riser?'_ However, he decided to man up. "Well...I am a man, so... Yes, I agree with you." He tried to sound dramatic, but it didn't really work.

"Do you want to go down on me?" Rias went on even further, with a naughty smile.

 _'WHHHAAAA?!'_ Issei couldn't believe what he was hearing. "I uh..."

Rias' voice was as sexy as ever. "I'm willing to do anything for you, as long as it makes you happy." She had completely forgotten about training that was supposed to commence later on.

Issei looked Rias in the eyes. _'ANYTHING!?'_

Rias then laid her body down on Issei's. "Let me feel you, Ise." She stared down at him with sexy eyes.

 _'O-Oh shit! All of the sensations of Buchou's body are being transmitted to my bodyyyy!'_ Issei's arms, chest, stomach, and legs were now in contact with Rias' soft and smooth skin. _'Her enormous breasts are compressed down against my chest, and the size and elasticity of it is amazing! Her breasts feel amazing on my chest! Damn, Buchou's body is still the best! It's smooth and so soft to the touch!'  
_

As they enjoyed each other's body feeling, their faces got closer. Their bodies got hotter. Rias then cupped Issei's cheeks and gave him a soft, passionate kiss on the lips. "Mmhm."

Issei's eyes widened. _'I received Buchou's kiss!? Uoooooooh! I-I am kissing Buchou once againnnnnnn! T-This, sensation of lips! To be able to taste it again! It's a soft and sensual contact!'_ After several seconds past, he closed his eyes too and returned the kiss to her with passion. _'This is awesome! I'm making out with Buchou, for cryin' out-loud!'_ His hands wandered to Rias' butt, and he squeezed it while kissing her.

Their latest kiss; it's not even the first time that they kissed. It was much longer than usual, and they kissed while doing it more gently. They have already kissed many times, but this time there is more passion in it.

Rias cuddled Issei tightly and french kissed him passionately. She slipped her tongue in his mouth and kissed even more. Saliva was being exchanged during the very passionate kiss. She snickered at the feeling of Issei touching her ass, their tongues intertwined.

 _'M-My tongue is being sucked by Buchou…!'_ Issei kissed the Devil beauty back deeply. _'Oh man, I'm not s-sure if I'm ready for this!'_ He prepared himself for whatever Rias would do next. He battled her tongue with his own, fighting for dominance. He continued squeezing Rias' soft butt. _'Her butt is so nice, too!'_ He swallowed down Rias' saliva which came inside his mouth as they kissed. He loved how wet and warm Rias' mouth was.

Rias gave Issei one last loving kiss and then rubbed her nose against his nose. After pulling away and opening her eyes, she said, "A little time to bond with my servant," seductively while pressing herself onto his chest. "Would you like to touch my chest?" She had a naughty smile.

Issei's eyes opened back up, and were now widened as he tried not to have a nosebleed. "O...O...Of course!" He drooled at her beauty.

Rias took Issei's waists and guided both hands to her large breasts. "You love my breasts, don't you?" She smirked a little.

Issei blushed madly and nodded. "They're incredible! The best!" He let his five fingers in both hands get absorbed by her large and soft breasts, enjoying the amazing sensation. ' _Aaah, this is it! This is Buchou's oppai! It's smooth, it's elasticity, it sticks forward, and it is very enormous and soft!'_ He controlled himself not to have a nosebleed. "They're incredible! The best!"

"Ahhh..." Rias looked at him with emotional eyes and muttered, "…Don't stop.''

He moved his hands slightly as they sinked in them. ' _Her soft and enormous boobies are stimulating my brain!'_ The bulge in his boxers was huge by this point. He could feel the weight pressing down on his hands. _'Oppai are amazing! They're soft, and I'm feeling 'em!'_

Rias made a seductive voice at the same time where she went "…Ah". She looked down at Issei. "Mhm... You always wanted to suck on them, haven't you?" She straddled him, making Issei's bulge go in-between her soft butt-cheeks. "...Go ahead."

Issei's eyes widened again as he felt the sensation of Rias' nicely shaped butt. _'Holy shit! Really?!'_ There was no way he could decline the offer. "O-Okay, here I go?" He leaned up and took Rias' left nipple in his mouth. He sucked on it, all the while squeezing and fondling her right breast. ' _I'm finally sucking her oppai!'_

Rias enjoyed Issei's activities. "Ahn~!" She shivered slightly at the feeling of her breasts being played with. She was still new to this sort of thing.

Issei continued on with playing with his most favorite things in the world. _'They're so soft, so elastic, so big! So damn amazing! I love them so much!'_ Once he was satisfied with the left breast, he switched to right nipple and sucked on it. He would frequently squeeze and fondle Rias' fantastic boobs as he alternated between sucking on each nipple.

Rias gasped and moaned in pleasure. "That's it Ise...!" She stroked his hair.

Issei then pressed both breasts together and sucked on both nipples at once. _'Boobies, breasts, boobs, tits, funbags, melons, marshmallows, I don't care what you call them! I love 'em!'_ Issei continued to suck on Rias' breasts while playing with them. He felt like never stopping, even if his life depended on it. "I love your breasts to death, Buchou!" He placed his face in-between her breasts and motorboated her.

Rias giggled. "Wow, you really do love my breasts, Ise!" She moaned in delight. However, she wanted to take control now. "It's time for me to give you pleasure." She didn't wait for a response and swiftly removed Issei's boxers. "I see that you're quite big." She then began to stroke his shaft. It was about 9 inches in length.

Issei had a big goofy look on his face while nodding excitedly. _'H-Holy shit! My junior is being touched by a woman! And it's by Buchou... I mean Rias, of all people! Damn, her hand is warm!'_ His hands were still sunk in her breasts _.  
_

Rias gave Issei the sexiest face she possibly could. "I know what to do next." She wrapped her nice, big tits around his hardened cock. "How does that feel? Do you like it?"

"Ga-agh...A-Ah!" Issei's nostrils were blowing out steam. The sensation was hard to describe, for it was too good for words! He always thought that simply feeling tits was good enough, until he experienced this particular event. ' _Uoooooooooooooooooooh! Buchou's oppai, ON MY COCK!? Soft, huge, smooth and elastic tits on my cock! No fucking way, dude!'_

"I'll take your moans as a 'yes'." Rias smirked at her servant. She squeezed Issei's cock inside her breasts and moved them up and down without restraint.

"B-Buchou! Let me-Whoaaaaa!" Issei closed his eyes tightly. ' _Aaah, Rias's oppai! Aaah, Rias's oppaaaai~!'_ He felt like he was drowning in a pleasure pool. _'So soft...so big... I can't handle it!'_

Rias pressed harder against Issei's cock and slid her breasts up and down faster. "Now you _really_ love my breasts, don't you?" Her voice was as sexy as can be. She continued her activity without stopping. "Ufufufu. Feel free to cum anytime."

 _'I'm having a breast-parade inside my head...! This. Is. Fucking. AWESOME!'_ He was speechless. Before he would answer, Issei had a load to drop off. "I'm gonna...I'm gonna-CUM! AHH-HNGGGHGHGHGH!" Issei's orgasm came and so did his cock; he shot lots of cum all over Rias' beautiful face. "Uwaaaaaaaaa!"

"You deserve it, Ise." Rias licked off the cum on her face. "This tastes good, as I suspected it would be..." She was extremely turned on. "Its time now, Ise... For the main course." She smiled at him.

Issei looked at Rias with a shocked face. _'...This is it! It's finally here! My first time!'_ He stared deeply into her eyes. "Are we seriously gonna...!?"

Rias laid on the bed, spreading her sexy legs. "There's no one else to take my virginity, except for you. Just you and only you, my Ise. Now come and make me yours, forever." She had a seductive smile.

 _'Oh fuck, dude!'_ Issei was happy beyond belief at the fact that it is only he who'll take her virginity. No other person, and that included Riser, can ever receive this privilege. _'Okay Issei, don't fuck this up! This could be your only chance to score! I want to have sex with Buchooooooooooou!"_ Issei got on top of Rias and pressed the tip of his cock against the labia. '... _But I believed that my first sex experience would be with Buchou!'_ He moved a little and widened her vulva, going in further. He then found the hymen, her barrier that indicates her being a virgin. _'Oh shit, is this really happening?!'_ He almost couldn't believe it. He would have pinched himself to make sure that he wasn't dreaming, but he was too occupied to even bother. _'Buchou...I mean, Rias being my first time is simply the best! There isn't anything more fortunate than this!'_

Rias secured around his waist with her legs. "Go ahead Ise, you're almost there."

Issei had nowhere to go but forward, so he thrusted forward to break through. ' _Uooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo!'_ The feeling was even harder to describe than previous activities. _'Holy fuck! I'm now officially a man!'_ Issei tried not to blow his load so early as he took in the new world of pleasure that he entered. _'I-I'm not sure that I can handle t-this...!_ ' He felt Rias' pussy tighten around his cock.

Rias winced from the pain, gritting her teeth. "Ouch...! It's s-so big!" She quivered and shook at the sensation of Issei's hard cock inside her.

Issei began to move slowly and was careful not to bring Rias too much pain. He took in the delightful sensations of her warmth and moist walls. _'I-I never felt anything else like this before...!'_ He moaned loudly during this whole session. He felt so powerful being someone who was banging Rias Gremory of all people. ' _I'm having sex with Rias...'_ Inside her holy ground, the melting folds of flesh contracted and wrapped around the invader as if guiding it deeper inside. There was no way he could run away now. No man would pull out here. He felt indescribable pleasure. "Aaaaaaaaah!"

Rias moaned loudly and screamed out Issei's name. ''You're so big! I... I can feel everything...!" The pain she initially felt was slowly turning into pleasure. She closed her eyes tightly as her body was heating up. "Ahh! I-Ise!"

"R-Rias, your pussy is so fuckin' amazing! So tight!" Issei now thrusted in her pussy hard, deep and fast, as if trying to win a non-existent competition. The insane pleasure he received from this was ridiculous. ' _Oh, she twitches inside when I squeeze her nipples!'_ He enjoyed how the internal flesh sucked at him, how warm the sticky fluids were, and how a wave of convulsions would occasionally leave her womb and pass through her tightened flesh. ' _Does this mean…we're a perfect match?'_

"Ah…wah. …Ahn…ahn!" Rias couldn't handle this intense sensation, and she let her cute voice out several times. "Ahh! Ise, I can't take this a-anymore! It's too g-good!" She grabbed the bed sheets, feeling great amounts of sheer pleasure by this point. "Nnnnn, ah...!" Her breasts bounced uncontrollably, tearing up to the pleasure.

Issei pounded away like a jackhammer, hitting Rias' g-spot. He had no idea how he was lasting so long. He also noticed that Rias' pussy got hotter and tighter the deeper his cock went in. "Rias, your p-pussy feels so damn amazing! I love it, along with your divine breasts!" He closed his eyes and played with Rias' large breasts while he pounded her more.

"A-Ahh! I can't take it!" Rias felt her orgasm approaching soon. She wailed and screamed in pleasure. "Keep g-going, Ise! Don't stop!" Rias felt Issei twitching inside her. She had her arms and legs wrapped around him tightly. "Cum inside my pussy! I want all of it! Don't hold back!" She was breathing heavily and her nipples hardened.

Issei thrusted balls deep in Rias hard and fast. "Oh fuck, Rias...you feel s-so good!" He was about to cum and picked up his pace. Issei had no choice except to unleash his load. "I'm c-cumming!" Issei plunged his cock deep inside Rias' pussy. "Hohoholy shit here it-CCCCCAAAAGGGGHHHH!" His eyes rolled into the back of his head while he experienced his best orgasm ever. "Agaaaaaaaah, Ggggggga!" He filled Rias' soft, tight, wet and hot pussy with lots of warm cum. "Arggghhh!" He grunted and moaned while shooting lengthy spurts of semen inside her pussy.

"H-H-Hnn! Oh my~!" Rias screamed as she felt Issei's cum rush inside her. The feeling made her have an intense orgasm next. "Ah, AH... AHHHHHNNN~!" Rias moaned loudly in ecstasy. "Yes! Yes~!" She arched backwards, squirting all over Issei's cock uncontrollably. After she was done, she dropped back down quickly.

Issei was speechless once finished. "W-Wow..." He then fainted on top of Rias.

Rias smiled and cuddled her servant in her arms. "Ise. I love you… I love you more than anyone else," she whispered in his ear. They cuddled together, peacefully.


End file.
